Original Air Date—14 September 2009
As the summer is drawing to a close, Blair and Chuck are madly in love and adjusting to their new "in a relationship" status, breaking all the traditional rules of dating as would be expected. Serena returns from her European adventure with many secrets to hide and a complicated relationship with Carter Baizen. Nate returns from his travels with a mysterious brunette, Bree Buckley in tow. Rufus, Dan and Jenny spent the summer in the Hamptons, adjusting to the van Der Woodsens' glamorous lifestyle surprisingly faster than any of them expected. Meanwhile, Vanessa begins a relationship with Scott, not knowing that is the lost brother of Dan and Serena.
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Season 3, Episode 2: The Freshmen
Original Air Date—21 September 2009
Blair, who is determined to maintain her Queen status in college, embarks on her first day at NYU, along with Dan and Vanessa. Unfortunately, Georgina turns up as Blair's roommate in the dorms, determined to make Blair a social outcast. As Serena prepares to depart for Brown, she and Chuck have a major falling out, so she recruits Chuck's enemy, Carter, to help her get even. Nate and Bree decide to explore their relationship further, knowing full well that it could cause tension between their families who are political rivals.
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Season 3, Episode 3: The Lost Boy
Original Air Date—28 September 2009
It's an Upper East Side face-off when Blair and Chuck both set their sights on a particular item up for bid at Sotheby's and the personal stakes are high. Serena suspects that Carter may be up to his old habits, Georgina takes an interest in Dan, and Vanessa begins to suspect that something isn't quite right with Scott.
Season 3, Episode 4: Dan de FleuretteOriginal Air Date—5 October 2009
On the first day of school at Constance Billard, Jenny is forced to make her rightful place as the new Queen Bee of the Mean Girls. Unfortunately for Jenny, Blair is more than happy to intervene when news reaches her that Jenny may need her help. Meanwhile, Lily finally returns home to Rufus and her family to find that things are definitely not as she left them, especially after learning that Serena has decided against going to Brown University. Elsewhere, a famous teenage movie actress, Olivia Burke, enrolls at NYU and is assigned as Vanessa's new roommate in which Olivia hopes for a somewhat normal college experience. Also, Olivia's best friend Ursula, another actress co-starring in Olivia's latest movie, befriends Serena.
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Season 3, Episode 5: Rufus Getting Married
Original Air Date—12 October 2009
Lily and Rufus decide to move up their wedding to the next day, but a series of complications threaten to tear them back apart again. Meanwhile, Chuck discovers a secret that Carter has been keeping from Serena which involves Nate's girlfriend Bree and her family whom are out to get Carter. Dan and Vanessa are pulled into one of Georgina's schemes when she threatens to ruin Lily and Rufus' wedding by revealing the secret about Scott Rosson as their illegitimate son. Also, Blair is suspicious of Bree and shares her concerns with Nate that she may have an agenda regarding him and Carter.
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Season 3, Episode 6: Enough About Eve
Original Air Date—19 October 2009
Vanessa and Blair both take to scheming to be given the honor of giving the freshman toast at NYU. Meanwhile, Serena and Nate try their hand at poker in hopes of winning Carter back from the Buckleys, and Dan wants to introduce Olivia to Rufus and Lily.
Season 3, Episode 7: How to Succeed in BassnessOriginal Air Date—26 October 2009
Chuck decides to move up his hotel nightclub's opening and enlists Serena's help to get the word out to her celebrity clients for publicity reasons. Feeling left out of the planning, Blair attempts to win Chuck's approval by secretly helping him with a problem concerning opening night. Meanwhile, Dan is unnerved when he finally watches one of Olivia's infamous simulated sex scenes in one of her movies with co-star and real-life boyfriend at the time, Patrick Robinson. Jenny is forced to choose between her friendship with Eric and her new role as Queen Bee of Constance Billiard since she and the Mean Girls are not required to have any friends, except the ones their own vicious and cynical circle. Elsewhere, Rufus gets Lily into the Halloween spirit by taking her out to a costume party.
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Season 3, Episode 8: The Grandfather: Part II
Original Air Date—2 November 2009
Olivia says something she regrets during her appearance on Jimmy Fallon's TV talk show and tries to keep Dan from finding out. With the local election day around the corner, Nate suspects that his grandfather will stop at nothing to get his cousin Trip elected to congress. In the midst of another feud with Serena, Blair befriends a new "it" girl and takes her to an election night party at Chuck's hotel, hoping to make Serena jealous.
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Season 3, Episode 9: They Shoot Humphreys, Don't They?
Original Air Date—9 November 2009
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Season 3, Episode 10: The Last Days of Disco Stick
Original Air Date—16 November 2009
Hoping to impress the elitist theater kids at NYU, Blair sets her sights on landing a private concert with the hottest musical performer of the year, Lady Gaga. Meanwhile, Dan and Olivia sign up to write and star in a school play, based on an idea by Blair and directed by Vanessa. With Blair out of the picture, Serena turns to Nate to help her get through a difficult situation. As a favor to Chuck, Jenny agrees to hang out with Damien, the son of an ambassador who is staying at Chuck's hotel, but the experience proves to be a lot more intriguing than she expected.
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Season 3, Episode 11: Treasure of Serena Madre
Original Air Date—30 November 2009
As Thanksgiving draws near, Blair suspects her mother, Eleanor, has been keeping a big secret from her, but it turns out to be something else entirely. Meanwhile, Vanessa is supposed to spend Thanksgiving with her parents, but has a fight with her picky and estranged mother and she ends up going to Dan's dorm room. Rufus discovers that Lily has been lying to him about the true nature of her mother Cece's health. Chuck tells Nate that he has some potentially damaging information about one of their friends. Elsewhere, Jenny learns that Eric was behind her very public embarrassment at Cotillion and can't pass up a chance to get even with him in the most cruel way, which makes her appear even more vile and twisted than everyone else around her. Also, Serena is put in a very awkward position when Lily invites Trip and his wife, Maureen, to join them for Thanksgiving dinner at their penthouse, and Maureen may know a lot more about what is going on between Trip and Serena than she claims to.
